EP0012834B1 - Acylamino-Gruppe enthaltende Aminoorganosilicium-Verbindungen - Google Patents

Acylamino-Gruppe enthaltende Aminoorganosilicium-Verbindungen Download PDF

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Publication number
EP0012834B1
EP0012834B1 EP79104517A EP79104517A EP0012834B1 EP 0012834 B1 EP0012834 B1 EP 0012834B1 EP 79104517 A EP79104517 A EP 79104517A EP 79104517 A EP79104517 A EP 79104517A EP 0012834 B1 EP0012834 B1 EP 0012834B1
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radical
hydrogen
formula
compound
carbon atoms
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EP0012834A2 (de
EP0012834A3 (en
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Enrico James Pepe
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Union Carbide Corp
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Union Carbide Corp
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/544—Silicon-containing compounds containing nitrogen
    • C08K5/5455—Silicon-containing compounds containing nitrogen containing at least one group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages

Definitions

  • This invention relates to novel aminoorganosilicon acylamino compounds.
  • Silicon containing polyazimide compounds are well known in the art as seen by U.S. Patent 3,746,738. However, such compounds contain at least two acylamino groups and at least one secondary and/or tertiary amino group in the same substituent radical.
  • the novel silicon compounds of this invention are distinguished from such polyazimide compounds in that they contain only a single acylamino group and at least one secondary and/or tertiary amino groups in the same substituent radical.
  • GB-A-882 059 is carbamylalkylalkoxysilanes as represented by the formula: wherein R and R' are hydrogen atoms, or alkyl or aryl radicals; R" is an alkyl or aryl radical; X is an alkoxy radical; a represents an integer of at least 2; and b is 0, 1 or 2.
  • R and R' are hydrogen atoms, or alkyl or aryl radicals
  • R" is an alkyl or aryl radical
  • X is an alkoxy radical
  • a represents an integer of at least 2
  • b is 0, 1 or 2.
  • the known products are suited as the thermosetting resins or for modifying thermosetting resins, as adhesives and sizes for fiber material.
  • Illustrative radicals represented by X above include alkoxy radicals having 1 to 6 carbon atoms, such as methoxy, ethoxy, propoxy, 2-methoxyethoxy, isopropoxy, hexyloxy and the like, the preferred alkoxy radicals being methoxy, ethoxy and 2-methoxyethoxy.
  • Illustrative divalent alkylene radicals represented by R above include methylene, ethylene, propylene, trimethylene, tetramethylene and the like, the preferred divalent alkylene groups being ethylene (-C 2 H 4 -) and trimethylene ( ⁇ C 3 H 6 ⁇ ).
  • Illustrative radicals represented by R' above include alkyl radicals such as methyl, ethyl, propyl, isopropyl, butyl and the like.
  • Illustrative divalent alkylene radicals represented by R 2 above include ethylene, propylene, trimethylene, tetramethylene and the like, the preferred divalent alkylene groups being ethylene and trimethylene.
  • Illustrative radicals represented by R 3 above include hydrogen, phenyl and alkyl radicals having from 1 to 20 carbon atoms such as methyl, ethyl, propyl, octyl, octadecyl ; eicosyl and the like.
  • R 3 is hydrogen.
  • Illustrative radicals represented by R 4 above include hydrogen (when x is at least 1), phenyl, alkyl radicals having from 1 to 20 carbon atoms such as methyl, ethyl, propyl, octyl, octadecyl, eicosyl, and the like as well as silyl groups of the formula wherein R and R', X and a are the same as defined above.
  • R 4 represents a silyl group.
  • Illustrative radicals represented by Q above include hydrogen, phenyl, alkyl radicals having from 1 to 4 carbon atoms such as methyl, ethyl, propyl, butyl and the like, as well as ester radicals of the formula wherein R 5 represents an alkyl radical having from 1 to 4 carbon atoms such as methyl, ethyl, propyl, butyl, and the like.
  • R 5 represents an alkyl radical having from 1 to 4 carbon atoms such as methyl, ethyl, propyl, butyl, and the like.
  • Q is hydrogen.
  • a is preferably O.
  • each individual radical or group represented by the above symbols may be the same or different in any given compound.
  • aminoorganosilicon acylamino compounds of this invention can be prepared by following simple processing procedures involving the use of Michael addition products as the starting materials.
  • aminosilane compounds of the formula wherein X, R, R', R 2 , R 3 , a and t are the same as defined above can be reacted with an olefinic carboxylate ester by the Michael addition method to form the corresponding amino-carboxylic acid ester of the silane and carboxylate materials employed as seen by the following illustration:
  • amino-carboxylic acid ester-silane intermediate product so formed can then be subsequently amidated with either (1) a primary amino silicon compound of Formula (II) above, (2) a primary organoamine, or (3) a primary organic polyamine to produce the desired aminoorganosilicon acylamino compounds of this invention depicted by Formula (I) above as seen by the following illustrations
  • amino-carboxylic acid ester containing silane compounds employable as the starting materials for such types of processes as depicted above and/or the Michael addition method for their preparation are well known in the art as seen for example by U.S. Patent 2,929,829 and may be illustrated by the following formula wherein R, R', R 2 , R 3 , Q, X, a and t are the same as defined above and R 6 is a monovalent hydrocarbon radical, preferably an alkyl radical having 1 to 4 carbon atoms such as methyl, ethyl, propyl, butyl, and the like.
  • Illustrative aminosilanes that can be employed in such a Michael addition process include those of Formula (II) above such as
  • the processing conditions of said Michael addition are well known and taught e.g. in U.S.P. 2,929,829 and in this instance, merely involve forming a mixture of about 1 mole of the aminosilicon compound and about one mole of the olefinic carboxylate compound and maintaining the mixture at a temperature, preferably about room temperature, until the aminosilicon compound has added to the double bond of the olefinic carboxate thereby producing the desired Michael addition product.
  • aminoorganosilicon acylamino compounds of this invention as shown in Formula (1) above can be produced by amidating an amino-carboxylic acid ester containing silane of Formula (III) above with either (1) a primary aminosilane compound of Formula (II) above; (2) a primary organic amine or (3) a primary organic polyamine.
  • Illustrative primary aminosilane reactants include those of the formula wherein R, R', R 2 , R 3 , X, a and t are the same as defined above such as
  • Illustrative primary organic amines include those of the formula wherein R 7 is an alkyl radical having from 1 to 20 carbon atoms or a phenyl radical, such as methylamine, ethylamine, propylamine, octylamine, octadecylamine, eicosylamine, aniline, and the like.
  • Illustrative primary organic polyamines include those of the formula wherein R 2 , R 3 R 4 and R 4 are the same as defined above, and b has a value of 1 to 4, such as
  • amidation processes will merely depend upon which type of silane product is desired and that all three of the above depicted amidation processes can be carried out merely by forming a mixture of a carboalkoxyalkylaminoorganosilane such as shown in Formula (III) above with any of the amino compounds shown in formulas (V), (VI) or (VII) above and maintaining the mixture at a temperature at which the carboalkoxy group and primary amino group react to produce the desired aminoorganosilicon acylamino compound.
  • the relative amounts of the two reactants used as the starting materials for said above amidation processes is not narrowly critical.
  • from one to ten chemical equivalents of primary amine starting materials of Formulas (V), (VI) or (VII) can be employed for each mole of the carboalkoxyalkyl- aminosilane of Formula III above.
  • an excess of such primary amine reactants is not desirable unless the unreacted excess can be readily removed from the reaction mixture or does not interfere with the intended use of the desired silane condensation product.
  • the amino starting material is an aminosilane of Formula (V) above or a primary amine of Formula (VI) above or a primary polyamine of Formula (VII) above that contains only one primary amino group it is preferred that the carboalkoxyalkyaminoorganosilane starting material be reacted with a stoichiometric amount (1 mole to 1 mole) of said amino starting materials.
  • the amino starting material is a primary polyamine of Formula (VII) above that contains two primary amino groups it is essential to employ a stoichiometric excess of said polyamine in order to avoid producing bis-silylated compounds containing more than a single acylamino group.
  • the aminoorganosilicon acylamino compounds of this invention by first forming the amino carboxylic acid ester containing silane intermediate of Formula (III) above and then reacting said intermediate with the primary amino starting material it is to be understood that, if desired the bis silylated compounds of this invention can also be prepared in a single step for example, by reacting an olefinic compound of Formula (IV) above that contains only one carboalkoxy group with a primary aminosilane of Formula (V) above using a mole ratio of 0.5 moles of the carboxylate compound to 1 mole of the aminosilane.
  • an olefinic carboxylate starting material which contains the same type of alkoxy group as the alkoxy radicals of the aminosilane starting material since when different alkoxy groups are involved (e.g. in the reaction of methyl acrylate and a triethoxy containing silane starting material the process can lead to a mixed methoxy-ethoxy silane adduct intermediate and/or an acylamino containing mixed methoxy-ethoxy silane product.
  • the above amidation processes may be carried out over a wide range of temperatures such as from 0°C to 200°C; however, it is generally preferred to employ a temperature in the range of from about 25°C to about 150°C.
  • the by-product alcohol may be removed by any conventional method such as by distillation and pressures other than atmospheric pressure may be used to aid in the removal of the alcohol if desired.
  • the aminoorganosilicon acylamino compounds of this invention can be employed in their crude product form or purified if desired after removal of the alcohol by any conventional method such as further distillation.
  • a catalyst to accelerate the condensation reaction (amidation) between the carboalkoxy group and primary amino group of the starting materials.
  • Illustrative catalysts which may be employed for this purpose are the tin catalysts described in U.S. Patent 2,890,208 as well as other metal catalysts such as those described in U.S. Patent 3,169,945.
  • aminoorganosilicon acylamino compounds of this invention include such compounds as and the like.
  • the most preferred aminoorganosilicon compounds of this invention are the bis-silyl compounds, especially
  • aminoorganosilicon acylamino compounds of this invention have a wide range of utility and may be employed in the same manner as conventionally known amino containing silanes.
  • they can be hydrolyzed and condensed with or without other conventional organosilanes to form polymeric siloxanes such as those containing the structural unit wherein R, R', R 2 , R 3 , Q, a t and x are the same as defined above and R S is an alkyl radical having 1 to 20 carbon atoms, a phenyl radical or a siloxy radical of the formula wherein R, R I and a are the same as defined above, with the proviso that when x is at least one R 4 can also be hydrogen; as well as copolymers and terpolymers containing at least one siloxy unit of Formula VIII above and at least one siloxy unit of the formula wherein R 9 represents a substituted or unsubstituted monovalent hydrocarbon radical and c has a value of 0 to 2, e
  • a dimethylsiloxy unit a dimethylsiloxy unit.
  • polymeric materials may be linear, branched or cyclic, and can be endblocked in any conventional manner desired, such as by siloxy units of the formula wherein X is a hydrolysable group, R'° is a substituted or unsubstituted monovalent hydrocarbon radical such as alkyl or aryl, d has a value of 0 to 3 and e has a value of 0 to 3, the sum of d + e being 3.
  • aminoorganosilicon acylamino compounds of this invention as well as the above described polymeric siloxanes may be used as sizes for fibrous materials, particularly fiberous glass materials in the same manner as heretofore conventional silicon coupling agents have been employed in combination with a broad variety of thermosetting and/or thermoplastic resins such as disclosed in U.S.P. 3,754,971.
  • Said silanes and siloxanes may also be used as coupling agents for other inorganic substances such as siliceous pigments and fillers, e.g. clay, silica, hydrated silica, fumed silica, sand and the like.
  • organoaminosilicon acylamino compounds of this invention are particularly useful additives for hydroxyl containing organic thermoplastic polymer compositions that result in room temperature curable coatings that provide protective and solvent resistant cured coatings for a wide variety of substrates such as metals, plastics, wood, cloth, foam, glass, and the like.
  • total methanol collected 90.2 grams, theory 80 grams
  • An amine analysis of said silane product showed 2.7 moles N/kg. (theory 2.42 moles titratable N/kg.).
  • a 500 ml., 3 neck flask having the same experimental set-up as described in Example 1 was charged with about 168.9 grams (0.53 moles) of (C 2 H 5 O) 3 Si(CH 2 ) 3 NH(CH 2 ) 2 COOC 2 H 5 , about 160.7 grams (0.53 moles) of octadecyl amine (88.9% pure by amine titration) and about 0.824 grams (0.25 weight percent) of dibutyl tin oxide catalyst and the stirred reaction mixture heated to a final temperature of about 160°C over a period of about 16 hours while removing 24.7 grams (0.53 moles) of 98.3% pure ethyl alcohol to produce the amber wax-like crude silane product An amine analysis of said silane product made by dissolving a 1 gram aliquot of the product in 25 ml.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)

Claims (11)

1. Aminoorganosilicium-acylamino-Verbindungen der Formel:
Figure imgb0059
worin X eine Alkoxygruppe mit 1 bis 6 C-Atomen; R eine Alkylengruppe mit 1 bis 4 C-Atomen; R' H oder eine Alkylgruppe mit 1 bis 4 C-Atomen; R2 eine Alkylengruppe mit 2 bis 4 C-Atomen; R3 H, eine Alkylgruppe mit 1 bis 20 C-Atomen oder eine Phenylgruppe; R4 eine Alkylgruppe mit 1 bis 20 C-Atomen, eine Phenylgruppe oder eine Silylgruppe der Formel:
Figure imgb0060
worin X, R und R' obige Bedeutung haben und Q H, eine Alkylgruppe mit 1 bis 4 C-Atomen, eine Phenylgruppe oder ein Esterrest -COOR5 ist, worin R5 eine Alkylgruppe mit 1 bis 4 C-Atomen Bedeutet und die Indices a einen Wert von 0 bis 2, t und x jeweils einen Wert von 0 bis 4 haben können mit der Maßgabe, daß-wenn x zumindest 1 ist-R4 auch H sein kann.
2. Verbindungen des Anspruchs 1, dadurch gekennzeichnet, daß R3 und Q H sind, t O der 1; x 0 und R4 ein Alkylgruppe ist.
3. Verbindungen nach Anspruch 1, dadurch gekennzeichnet, daß R3 und Q H sind und t 0 oder 1 und x 1 und R4 H oder eine Alkylgruppe sind.
4. Verbindungen nach Anspruch 1, dadurch gekennzeichnet, daß R3 und Q H sind, t 0 oder 1 und x 0 ist und R4 eine Silylgruppe der Formel:
Figure imgb0061
bedeutet, worin R, RI und X sowie a die in Anspruch 1 gegebene Bedeutung besitzen.
5. Verbindungen nach Anspruch 4, dadurch gekennzeichnet, daß in der Verbindung a und t 0 sind, R -CH2CH2CH2- und X eine Methoxy-, Äthoxy- oder 2-Methoxyäthoxygruppe bedeutet.
6. Verbindungen nach Anspruch 5, dadurch gekennzeichnet, daß X eine Methoxygruppe ist.
7. Verbindungen nach Anspruch 5, dadurch gekennzeichnet, daß X eine Äthoxygruppe ist.
8. Verbindungen nach Anspruch 1, dadurch gekennzeichnet, daß R und Q H sind, t 0 oder 1 und x 1 sind, während R4 eine Silylgruppe der Formel:
Figure imgb0062
bedeutet, worin R, RI und X sowie a die in Anspruch 1 gegebene Definition haben.
9. Verbindungen nach Anspruch 8, dadurch gekennzeichnet, daß in der Formel der Verbindunq a 0, t, 1, R -CH2CH2CH2-, R2 -CH2CH2- und X eine Methoxy-, Äthoxy- oder 2-Methoxyäthoxygruppe ist.
10. Verbindungen nach Anspruch 9, dadurch gekennzeichnet, daß X eine Methoxygruppe ist.
11. Verbindungen nach Anspruch 9, dadurch gekennzeichnet, daß X eine Äthoxygruppe ist.
EP79104517A 1978-12-29 1979-11-15 Acylamino-Gruppe enthaltende Aminoorganosilicium-Verbindungen Expired EP0012834B1 (de)

Applications Claiming Priority (2)

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US974615 1978-12-29
US05/974,615 US4209455A (en) 1978-12-29 1978-12-29 Aminoorganosilicon acylamino compounds

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EP0012834A3 EP0012834A3 (en) 1980-07-23
EP0012834B1 true EP0012834B1 (de) 1982-05-05

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EP (1) EP0012834B1 (de)
JP (1) JPS5592393A (de)
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DE (1) DE2962740D1 (de)

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JPS6141518B2 (de) 1986-09-16
EP0012834A2 (de) 1980-07-09
CA1155452A (en) 1983-10-18
EP0012834A3 (en) 1980-07-23
DE2962740D1 (de) 1982-06-24
US4209455A (en) 1980-06-24
JPS5592393A (en) 1980-07-12

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